Ethanolamine → HCID 20508555, compound

HRID 1758779Notes

Reaction equation

HRID 1758779 reaction equation
Cl[CH:2](Cl)[CH3:3].FC1C=CC=CC=1C1C2C=C(N=C=O)C=CC=2N2C(C)=NN=C2CN=1.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[C:43]2[CH:44]=[C:45]([NH:48][C:49]([NH:51][CH2:52][CH2:53][OH:54])=[O:50])[CH:46]=[CH:47][C:42]=2[N:41]2C=[N:56][N:57]=[C:40]2[CH2:39][N:38]=1.NC1C=CC2N3C(C)=NN=C3CN=C(C3C=CC=CC=3F)C=2C=1.C(=O)([O-])[O-].[Na+].[Na+].C(CN)O>C(#N)C>[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[C:43]2[CH:44]=[C:45]([NH:48][C:49]([NH:51][CH2:52][CH2:53][OH:54])=[O:50])[CH:46]=[CH:47][C:42]=2[N:41]2[C:2]([CH3:3])=[N:56][N:57]=[C:40]2[CH2:39][N:38]=1

Participants

8

Reactant 6

HCID 700EthanolamineHCID 63651,1-DichloroethaneHCID 10340Sodium CarbonateHCID 20508545HCID 20508545, compoundHCID 205085528-Amino-6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepineHCID 20508556HCID 20508556, compound

Product 1

HCID 20508555HCID 20508555, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A dichloroethane solution of [6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-isocyanate, prepared as described in paragraph (a) of Example 1 from 5 g (16.3 mmol) of 8-amino-6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine, is added dropwise at room temperature while stirring to a suspension of 6.2 g (58.5 mmol) of sodium carbonate in 3 ml (49.8 mmol) of ethanolamine and 40 ml of acetonitrile. After 20 hours, the mixture is partitioned between 500 ml of water and 500 ml of methylene chloride/ethanol (4:1) at 50° C. The separated aqueous phase is treated again in an analogous manner, the combined organic extracts are dried and concentrated in vacuo. Crystallisation of the residue from ethanol yields 1-[6-(o-fluorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepin-8-yl]-3-(2-hydroxyethyl)urea of melting point 228°-230° C.

Workup

  1. additionis added dropwise at room temperature
  2. customthe mixture is partitioned between 500 ml of water and 500 ml of methylene chloride/ethanol (4:1) at 50° C
  3. additionThe separated aqueous phase is treated again in an analogous manner
  4. customthe combined organic extracts are dried
  5. concentrationconcentrated in vacuo
  6. customCrystallisation of the residue from ethanol

Sources & evidence

ORD record
ord-f7aba7b1c0f8454db2c45f1650b68ebb
Source dataset
uspto-grants-1983_02
Patent number
US04374773

Reaction notes

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